Apartments in Province of Siena and Villas – Holiday Lettings - Holiday Rentals Province of Siena

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Province of Siena

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6,810 Holiday homes

(2) Excellent 

22

Siena holiday apartment rental

Province of Siena / Siena

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 80 km
  • Child friendly
  • Car not necessary

from £152 / night

£1,060 / week

Book View

Responds fast!
avg. 3 hours 11 minutes

Booked 100+ times!

from £152 / night

(12) Excellent 

10

Holiday townhouse with swimming pool in Sovicille

Province of Siena / Sovicille

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

from £98 / night

£683 / week

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Booked 20+ times!

from £98 / night

43

San Gimignano holiday b&b accommodation

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £49 / night

£342 / week

Book View

Booked 8 times

from £49 / night

(1) Very Good 

18

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £120 / night

£887 / week

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from £120 / night

(2) Excellent 

34

Contignano holiday home rental

Radicofani / Contignano

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £62 / night

£355 / week

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Responds fast!
avg. 3 hours 0 minutes

Booked 10+ times!

from £62 / night

(5) Excellent 

21

Holiday villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

from £134 / night

£891 - £2,048 / week

Book View

Responds fast!
avg. 1 hour 3 minutes

Booked 20+ times!

from £134 / night

(4) Excellent 

36

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Private garden

from £152 / night

£1,024 - £1,653 / week

Book View

Booked 30+ times!

from £152 / night

17

Ski apartment to rent in Abbadia San Salvatore

Province of Siena / Abbadia San Salvatore

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Ski
  • Child friendly
  • Private garden

from £80 / night

£444 / week

Book View

Responds fast!
avg. 2 hours 35 minutes

from £80 / night

8

Holiday apartment rental

Province of Siena / Sarteano

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
  • Private garden

from £67 / night

£380 / week

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from £67 / night

(5) Very Good 

16

Contignano holiday apartment rental

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly

from £71 / night

£355 / week

Book View

Responds fast!
avg. 3 hours 0 minutes

Booked 10+ times!

from £71 / night

(2) Excellent 

99

Holiday villa with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £111 / night

£701 - £1,047 / week

Book View

Booked 9 times

from £111 / night

44

Holiday villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

6 13 1 night min

  • 6 bedrooms
  • sleeps 13
  • 1 night min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £494 / night

£3,459 - £5,277 / week

Book View

Booked 40+ times!

from £494 / night

14

Macciano holiday farmhouse rental

Chiusi / Macciano

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly

from £107 / night

£621 - £807 / week

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from £107 / night

(2) Excellent 

41

Holiday villa with swimming pool in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £273 / night

£1,909 - £2,672 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

Booked 4 times

from £273 / night

(2) Excellent 

29

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £311 / night

£1,597 - £2,306 / week

Book View

Booked 30+ times!

from £311 / night

(1) Excellent 

49

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Montegabbro

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets

from £54 / night

£311 - £435 / week

Book View

from £54 / night

(3) Excellent 

22

Holiday apartment with shared pool in Le Piazze

Province of Siena / Le Piazze

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £64 / night

£444 - £710 / week

Book View

from £64 / night

(50) Excellent 

Certificate of Excellence

25

Holiday home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Beautiful property in a stunning location” We stayed at Il Granario during the first two weeks of July, having also stayed there for two weeks in September 2011. The location is perfect, surrounded by beautiful rolling Tuscan countryside, with the sound of the warm breeze being the loudest noise you will hear much of the time. The house itself is lovely with a well equipped kitchen and the added bonus of both Sky television and an Internet connection. The outside space is a good size, with the communal pool just a few steps away, and the perfect position for viewing the amazing sunsets which occur almost every evening. Both San Gimignano and Volterra are beautiful places to visit, you can sit and people watch or just wander the medieval streets. Driving to Certaldo to catch the train ro Florence and Sienna is easy and much simpler than driving. On both occasions we have stayed at Il Granario I have gone out horse riding at a local stables, Agriturismo Maneggio, which is a beautiful and inexpensive way to see the Tuscan countryside (I have left the details at Il Granario for future guests reference). The service we received from Steve was excellent on both occasions we have stayed at Il Granario, with great ideas for excursions included in the folder at the house. Overall my wife and I would highly recommend Il Granario, the perfect place for rest and relaxation in a stunning location.

Certificate of Excellence

from £90 / night

£625 - £900 / week

Book View

Booked 40+ times!

from £90 / night

(9) Excellent 

132

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

10 20 min stay varies

  • 10 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £798 / night

£2,946 - £4,734 / week

Book View

from £798 / night

8

San Gusme holiday apartment rental

Castelnuovo Berardenga / San Gusme

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

from £66 / night

£460 / week

Book View

Booked 4 times

from £66 / night

(2) Excellent 

32

Holiday apartment in Cetona

Province of Siena / Cetona

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Child friendly

from £54 / night

£343 / week

Book View

from £54 / night

(2) Very Good 

12

Holiday apartment accommodation

Province of Siena / Radicofani

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £187 / night

£1,304 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from £187 / night

(1) Excellent 

49

Siena holiday villa rental

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £311 / night

£1,996 - £3,769 / week

Book View

from £311 / night

(2) Excellent 

16

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 3 3 nights min

  • 2 bedrooms
  • sleeps 3
  • 3 nights min
  • Suitable for children age 5+

from £67 / night

£401 / week

Book View

Responds fast!
avg. 41 minutes

Booked 30+ times!

from £67 / night

12

Holiday apartment rental

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £116 / night

£621 / week

Book View

from £116 / night

13

Radda in Chianti holiday apartment rental

Province of Siena / Radda in Chianti

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £89 / night

£535 - £802 / week

Book View

Responds fast!
avg. 47 minutes

from £89 / night

(3) Excellent 

13

Holiday apartment in Rapolano Terme

Province of Siena / Rapolano Terme

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly
  • Private garden

from £71 / night

£497 / week

Book View

from £71 / night

(4) Excellent 

16

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £106 / night

£531 - £751 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

Booked 4 times

from £106 / night

(24) Excellent 

26

Holiday cottage in San Gimignano

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • sleeps 5
  • 6 nights min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly

from £54 / night

£373 / week

Book View

Responds fast!
avg. 35 minutes

Booked 20+ times!

from £54 / night

22

Farmhouse letting in Gallina with shared pool

Province of Siena / Gallina

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool

from £57 / night

£399 - £699 / week

Enquire View

from £57 / night

40

Holiday apartment with shared pool in Vagliagli

Castelnuovo Berardenga / Vagliagli

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Pet friendly

from £67 / night

£321 - £557 / week

Book View

Responds fast!
avg. 2 hours 14 minutes

from £67 / night

(2) Excellent 

21

Holiday farmhouse with shared pool in Radicondoli

Province of Siena / Radicondoli

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £54 / night

£357 - £731 / week

Book View

from £54 / night

(9) Excellent 

56

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

from £399 / night

£2,439 / week

Book View

Booked 20+ times!

from £399 / night

(1) Excellent 

18

Holiday apartment rental

Province of Siena / Montepulciano

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £54 / night

£364 - £674 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

Booked 70+ times!

from £54 / night

(1) Excellent 

7

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

4 4 min stay varies

  • 4 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £62 / night

£373 - £577 / week

Book View

Booked 4 times

from £62 / night

(5) Excellent 

28

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £50 / night

£345 - £1,017 / week

Book View

Responds fast!
avg. 2 hours 37 minutes

Booked 20+ times!

from £50 / night

(2) Excellent 

14

Holiday apartment in Monticiano

Province of Siena / Monticiano

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets

from £54 / night

£357 / week

Book View

from £54 / night

(1) Excellent 

23

Holiday villa in Trequanda

Province of Siena / Trequanda

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £133 / night

£931 / week

Book View

from £133 / night

33

Montalcino holiday villa rental

Province of Siena / Montalcino

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £178 / night

£1,242 / week

Book View

Responds fast!
avg. 2 hours 47 minutes

Booked 10+ times!

from £178 / night

36

Holiday villa in Siena

Province of Siena / Siena

11 22 min stay varies

  • 11 bedrooms
  • sleeps 22
  • min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

from £488 / night

£2,661 - £4,434 / week

Book View

Booked 50+ times!

from £488 / night

Top Destination reviews

Amazing Tuscan holiday apartment in the historical Town centre of Colle di Val d'Elsa, sleeps 4
Ideal base in Tuscany

We spent three weeks here and loved living in the heart of the old town. The flat is well-equipped, sheets and towels are good quality, and it is light and spacious. For English guests it would be a good idea to provide a kettle and toaster! There is a car park below the house only a few minutes away, although you need to walk up a fairly steep slope to get back. The second set of stairs up to the flat is also quite steep: my husband walks with crutches and found it a challenge...There is a big Co-op down in the modern town (nothing like the English Co-op!) which has everything but the local bread shop, butcher and greengrocer a few doors away are good. The cake shop further up the road is amazing. Several good restaurants in the old town as well. Antonella and Giorgio are wonderful hosts: willing to help whenever you need it but also leave you to enjoy your holiday. They met us on arrival at Poggibonsi station and took us back there at the end of our holiday. We would certainly go again.see more
Luxury Villa for large group with private pool tennis court 15.000 mq of propert
Above and Beyond Expectation!

We cannot say enough great things about Villa di Leonardo, and the wonderful hosts, Maria and Roberto. From the beginning stages of planning our stay to the execution of our rehearsal dinner and wedding ceremony, everything was beyond incredible. The villa, which sleeps 20+ comfortably, sits on the most piece of property. Overlooking the tuscan hillsides and mountains, with an olive grove in the distance, a wonderful in-ground pool, and plenty of room to roam and explore. The property boasts the most gorgeous landscape and backdrop for a wedding, or any event. It's in a nice secluded area, but only a short distance into town for groceries and restaurants. There's also a phenomenal restaurant just down the road, which Maria made reservations for us on our first night. As if the villa and landscape weren't enough, you then have these two fabulous hosts in Maria and Roberto, who made sure every part of our wedding week was special. They helped plan a private wine tour, our amazing rehearsal dinner, and wedding dinner and events. They brought in a chef to prepare us an authentic pizza dinner, in the brick oven on the property, for our rehearsal. Our wedding dinner was an incredible feast, fit for royalty. We didn't have to worry about a thing. The history of the house is so fascinating, and Roberto was thrilled to tell us everything he knew about the property and surrounding area, making our wedding location even more special. If you are even considering Italy for your wedding, or any event, we HIGHLY recommend Villa di Leonardo. It's everything you could hope for, and so much more. We will be eternally grateful to Maria and Roberto for making our wedding the most amazing and beautiful day we could have ever had.see more
Rustic home Il Torrione, private garden and pool
Hidden gem

This place is amazing ! Cosy , homely . The pool and views are great and we really enjoyed our week here ! The owners Elise and mama were great and a brought us a midweek treat if a home cooked Italian stew ! Thank you ❤️ the pool and amenities are of an amazingly high standard and you really feel like you just want to stay in all day to enjoy the views the pool and the feel of the place , so relaxing . We explored the Tuscany hills and country side and has some great days out Florence , Pisa, were great and our favourite aaa Volterra . Don't forget your mosquito spray and take some food for breakfast as shops are closed in radicondoli on a Sunday , we would def go back here it was a really good high quality home see more
Apartment Valentina countryside not far from Siena
Relaxation Plus

We were a party of six, two couples and two singles. We made full use of the four spacious bedrooms and four bathrooms - no waiting for anyone. The owners could not have been more helpful or generous. They helped us with local info and someone visited the property every day but were always unobtrusive. The drive into Siena takes about 35 minutes but becomes easier each time. The benefit is peace, quiet and relaxation from the busy world. There are restaurants supermarkets and ATM all less than 15 minutes drive. The kitchen facilities are great with all the appliances you need including dishwasher. The laundry provides two washers and two dryers.see more
Rosia Village Apartment
Great location, highly raccomended

We loved this place! The apartment is super clean and central. Very closed to Siena, perfect for holidays or just few days of relax! Highly raccomended, def. we will be back soon! Thanks you for everything!!!!! … see more
charming cottage in peaceful country setting sleeps 2-6
We will come back!

It was great staying here! We found a nice little place to feel at home. The cottage is lovely furnished, very clean and has everything we needed for the week (including fast heating for some rainy and cold evenings (20minutes was enough to get the humid air out!) and free Wi-Fi, thats working perfectly and fast). We really loved sitting in the beautiful garden full of roses, looking over the wine-yards and listening to all the birds (also nightingales!!!). The cottage is set in a great surrounding - Tuscany like in a picture book! Laura was a perfect host. We felt very welcomed, we could ask her for everything and she could give us good hints for restaurants, hiking-paths and everything else you need to know for holiday. Thank you very much, Laura!see more